Hydrochloric Acid → HCID 70360055, compound

HRID 1650049Notes

Reaction equation

HRID 1650049 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C@@H:17]1[CH2:22][CH2:21][CH2:20][C:19](=O)[C@H:18]1[CH2:24][CH2:25][CH2:26][OH:27].O.NN.[OH-].[K+].Cl>CCOCC.C(O)CO>[OH:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:15])([CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:24][CH2:25][CH2:26][OH:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 70359964HCID 70359964, compound

Product 1

HCID 70360055HCID 70360055, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.9 g. (5.08 mmoles) of trans-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-2-(3-hydroxypropyl)cyclohexanone and 10.2 ml. of hydrazine hydrate in 20 ml. of ethylene glycol is heated at 100° C. for an hour. The reaction was cooled to 60° C. and 4.05 g. (72.3 mmoles) of solid potassium hydroxide added. The resultant mixture was heated for 2 hours at 200° C., then cooled and added to 500 ml. 1N hydrochloric acid and 300 ml. ether. The ether extract was washed with 300 ml. saturated sodium chloride, 300 ml. saturated sodium bicarbonate, dried over magnesium sulfate and evaporated under reduced pressure (aspirator) to an oil. The crude oil was purified via column chromatography on 100 g. of silica gel eluted with 70% ether-hexane to yield 406 mg. (22%) of the title compound as an oil.

Workup

  1. additionA mixture of 1.9 g
  2. temperaturecooled
  3. additionadded to 500 ml
  4. extractionThe ether extract
  5. washwas washed with 300 ml
  6. dry with materialsaturated sodium bicarbonate, dried over magnesium sulfate
  7. customevaporated under reduced pressure (aspirator) to an oil
  8. customThe crude oil was purified via column chromatography on 100 g
  9. washof silica gel eluted with 70% ether-hexane
  10. customto yield 406 mg

Sources & evidence

ORD record
ord-dfabebf0807b4be29215645c804974a5
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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